Spacious Bi Level home in the Perfect Chesterton Location! Westchester South offers quiet streets lined with mature trees, close to all Chesterton has to offer. This tastefully updated 4 Bedroom, 3 Bath home offers Real Hardwood floors, Updated Kitchen with Island and Pantry, Updated Bathrooms throughout, Primary Ensuite, Inviting Living room with Gas Fireplace.Outback enjoy a sweet deck looking over the fenced yard. Furnace, A/C and sump pump new in 2026! Roof new in 2019, windows 2022!

4 Beds ⋅ 3 Baths

Spacious Bi Level home in the Perfect Chesterton Location! Westchester South offers quiet streets lined with mature trees, close to all Chesterton has to offer. This tastefully updated 4 Bedroom, 3 Bath home offers Real Hardwood floors, Updated Kitchen with Island and Pantry, Updated Bathrooms throughout, Primary Ensuite, Inviting Living room with Gas Fireplace.Outback enjoy a sweet deck looking over the fenced yard. Furnace, A/C and sump pump new in 2026! Roof new in 2019, windows 2022!

301 Primrose Circle, Chesterton

$585,000

Welcome Home to space, comfort, and community await you at 2941 Nautica Drive. This exceptional 5-6 Bedroom, 4 bathroom, single-family home features over 4,500 square feet of functional living space designed for a modern lifestyle. A massive kitchen, oversized island, dining area, living room with fireplace and 2 bedrooms on the main level. 2nd level offers oversized main bedroom suite with Full bathroom and walk-in closets and 3 additional bedrooms. 3rd level offers a bonus room (currently used as a bedroom). Enjoy a large 0.44-acre yard perfect for outdoor fun, an attached 3 car garage with ample storage nestled within a highly desired neighborhood, this home is a rare find. Priced Below Market value, carpet and painting needed. Call today for a private showing.

5 Beds ⋅ 5 Baths

Welcome Home to space, comfort, and community await you at 2941 Nautica Drive. This exceptional 5-6 Bedroom, 4 bathroom, single-family home features over 4,500 square feet of functional living space designed for a modern lifestyle. A massive kitchen, oversized island, dining area, living room with fireplace and 2 bedrooms on the main level. 2nd level offers oversized main bedroom suite with Full bathroom and walk-in closets and 3 additional bedrooms. 3rd level offers a bonus room (currently used as a bedroom). Enjoy a large 0.44-acre yard perfect for outdoor fun, an attached 3 car garage with ample storage nestled within a highly desired neighborhood, this home is a rare find. Priced Below Market value, carpet and painting needed. Call today for a private showing.

2941 Nautica Drive, Chesterton

$314,900

Great location right in the heart of Duneland, near the new YMCA Healthy Living Campus! This move-in ready ranch features 4 bedrooms, 2.5 baths, a brand-new roof, and new gutters for total peace of mind. Step inside to a bright, inviting living room with oversized windows that flood the space with natural light and highlight the newly refinished wood floors flowing into the office area. The entire home is freshly painted and welcoming. The highly functional kitchen boasts a center island, abundant cabinet space, and generous countertops. Just off the kitchen, the spacious dining room easily accommodates all your entertaining needs, while a versatile flex room makes a perfect home office or playroom. Cozy up in the expansive great room featuring a custom-built fireplace--ideal for cool winter nights. As an added perk, you'll find a cable-ready bonus room above the garage, offering the ultimate media room, teen hangout, or secluded retreat!

4 Beds ⋅ 3 Baths

Great location right in the heart of Duneland, near the new YMCA Healthy Living Campus! This move-in ready ranch features 4 bedrooms, 2.5 baths, a brand-new roof, and new gutters for total peace of mind. Step inside to a bright, inviting living room with oversized windows that flood the space with natural light and highlight the newly refinished wood floors flowing into the office area. The entire home is freshly painted and welcoming. The highly functional kitchen boasts a center island, abundant cabinet space, and generous countertops. Just off the kitchen, the spacious dining room easily accommodates all your entertaining needs, while a versatile flex room makes a perfect home office or playroom. Cozy up in the expansive great room featuring a custom-built fireplace--ideal for cool winter nights. As an added perk, you'll find a cable-ready bonus room above the garage, offering the ultimate media room, teen hangout, or secluded retreat!

419 S 9th Street, Chesterton

$360,000

Welcome to this beautifully maintained 3-bedroom, 2.5-bath home in desirable Olde Towne Square! This spacious 2-story home offers an open-concept main level with a generous kitchen featuring ample cabinet and counter space, newer electric stove with a gas hookup for added flexibility, and easy flow into the dining and living areas. The upper level features a large primary suite with walk-in closet and private bath, along with two additional bedrooms and a full bath. Enjoy the convenience of an attached 2-car garage with extra 8' x 8' storage/workspace in the back, providing additional room beyond the standard garage footprint. The home also features a furnace that is approximately 1 year old and gas piping already in place for a future fireplace, offering the opportunity to add a fireplace down the road. Finished basement space provides even more flexibility for a recreation room, home office, or additional living space and is already stubbed for a future bathroom, making it easy to customize the space to fit your needs. Conveniently located near shopping, dining, schools, parks, major highways, and train transportation to Chicago, making commuting to the city a breeze. Schedule your showing today!

3 Beds ⋅ 3 Baths

Welcome to this beautifully maintained 3-bedroom, 2.5-bath home in desirable Olde Towne Square! This spacious 2-story home offers an open-concept main level with a generous kitchen featuring ample cabinet and counter space, newer electric stove with a gas hookup for added flexibility, and easy flow into the dining and living areas. The upper level features a large primary suite with walk-in closet and private bath, along with two additional bedrooms and a full bath. Enjoy the convenience of an attached 2-car garage with extra 8' x 8' storage/workspace in the back, providing additional room beyond the standard garage footprint. The home also features a furnace that is approximately 1 year old and gas piping already in place for a future fireplace, offering the opportunity to add a fireplace down the road. Finished basement space provides even more flexibility for a recreation room, home office, or additional living space and is already stubbed for a future bathroom, making it easy to customize the space to fit your needs. Conveniently located near shopping, dining, schools, parks, major highways, and train transportation to Chicago, making commuting to the city a breeze. Schedule your showing today!

803 Olde Towne Square, Chesterton

$354,900

Move-in ready and loaded with updates, this turn-key tri-level offers the space, style, and location today's buyers are searching for. Situated in the award-winning Duneland School District, you'll enjoy being just minutes from downtown Chesterton, the Indiana Dunes National Park, Lake Michigan beaches, the South Shore Line, Coffee Creek Preserve, shopping, dining, and major commuter routes. Inside, the sunny living room welcomes you with fresh paint & neutral decor The country kitchen features brand-new quartz countertops, a pantry, a full appliance package, and sliding door access to the backyard--perfect for everyday living and entertaining. The lower level adds valuable flexible space with brand-new carpet, a cozy brick fireplace, a fourth bedroom, a 3/4 bath, dedicated laundry room, and plenty of storage. Upstairs, retreat to a spacious primary bedroom along with two additional bedrooms and an updated full bath featuring new quartz countertops. Step outside to enjoy the freshly painted deck with a Sunsetter shade, a storage shed, and a generous backyard with room for gardening, pets, play, or outdoor gatherings. The heated 2.5-car garage provides ample space for vehicles, hobbies, and extra storage. Recent updates include new paint, new carpet, new quartz countertops in the kitchen and bathrooms, updated fixtures, and a new HVAC system (2022), making this home truly move-in ready. Schedule your private showing today!

4 Beds ⋅ 2 Baths

Move-in ready and loaded with updates, this turn-key tri-level offers the space, style, and location today's buyers are searching for. Situated in the award-winning Duneland School District, you'll enjoy being just minutes from downtown Chesterton, the Indiana Dunes National Park, Lake Michigan beaches, the South Shore Line, Coffee Creek Preserve, shopping, dining, and major commuter routes. Inside, the sunny living room welcomes you with fresh paint & neutral decor The country kitchen features brand-new quartz countertops, a pantry, a full appliance package, and sliding door access to the backyard--perfect for everyday living and entertaining. The lower level adds valuable flexible space with brand-new carpet, a cozy brick fireplace, a fourth bedroom, a 3/4 bath, dedicated laundry room, and plenty of storage. Upstairs, retreat to a spacious primary bedroom along with two additional bedrooms and an updated full bath featuring new quartz countertops. Step outside to enjoy the freshly painted deck with a Sunsetter shade, a storage shed, and a generous backyard with room for gardening, pets, play, or outdoor gatherings. The heated 2.5-car garage provides ample space for vehicles, hobbies, and extra storage. Recent updates include new paint, new carpet, new quartz countertops in the kitchen and bathrooms, updated fixtures, and a new HVAC system (2022), making this home truly move-in ready. Schedule your private showing today!

2342 Westwood Lane, Chesterton

$875,000

Step into a timeless masterpiece where history, craftsmanship, and tradition come together in one of Chesterton's most iconic neighborhoods. Proudly positioned at the heart of this cherished community on ONE ACRE this extraordinary three-story residence has been lovingly preserved while offering the space and amenities desired for modern living. Rich in architectural character, the home showcases stunning original details including exquisite tilework, handcrafted wood paneling, custom cabinetry, and elegant millwork that speak to a bygone era of unparalleled craftsmanship. Grand entertaining spaces include a stately formal dining room, a classic butler's pantry, and beautifully proportioned living areas designed for memorable gatherings. Offering 5 spacious bedrooms and 5 baths, the home seamlessly blends historic elegance with exceptional comfort. A rare indoor pool provides year-round enjoyment, while the enchanting English garden creates a private sanctuary of manicured beauty and quiet reflection. More than a home, this is a time honored property--a place where generations have celebrated holidays, hosted gatherings, and created lasting memories. Opportunities to own a residence of this significance are exceptionally rare. For those who appreciate history, timeless architecture, and the privilege of becoming the next steward of an extraordinary legacy, this is truly a once-in-a-lifetime offering.

5 Beds ⋅ 5 Baths

Step into a timeless masterpiece where history, craftsmanship, and tradition come together in one of Chesterton's most iconic neighborhoods. Proudly positioned at the heart of this cherished community on ONE ACRE this extraordinary three-story residence has been lovingly preserved while offering the space and amenities desired for modern living. Rich in architectural character, the home showcases stunning original details including exquisite tilework, handcrafted wood paneling, custom cabinetry, and elegant millwork that speak to a bygone era of unparalleled craftsmanship. Grand entertaining spaces include a stately formal dining room, a classic butler's pantry, and beautifully proportioned living areas designed for memorable gatherings. Offering 5 spacious bedrooms and 5 baths, the home seamlessly blends historic elegance with exceptional comfort. A rare indoor pool provides year-round enjoyment, while the enchanting English garden creates a private sanctuary of manicured beauty and quiet reflection. More than a home, this is a time honored property--a place where generations have celebrated holidays, hosted gatherings, and created lasting memories. Opportunities to own a residence of this significance are exceptionally rare. For those who appreciate history, timeless architecture, and the privilege of becoming the next steward of an extraordinary legacy, this is truly a once-in-a-lifetime offering.

229 E Morgan Avenue, Chesterton

Listing Leaders

Search

Resources

About